


Dress to Impress (Yourself)

by servilesammy



Category: Supernatural
Genre: Crossdressing, Crossdressing Sam Winchester, Feminization, Feminized Sam Winchester, Fluff, Gen, My First Fanfic, Sam is 15, Young Dean Winchester, Young Sam Winchester, first time wearing a dress
Language: English
Status: Completed
Published: 2018-07-13
Updated: 2018-07-13
Packaged: 2019-06-10 01:04:53
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 743
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15280188
Author URL: https://archiveofourown.org/users/servilesammy/pseuds/servilesammy
Summary: Sam Winchester is 15 years old and in his long-fingered hands he clutches a blushing pink sundress. Just the vague thought of the dress caressing his skin causes the blood to rise to his cheeks.Or:Sam's first time wearing a dress.





	Dress to Impress (Yourself)

Sam Winchester is 15 years old and in his long-fingered hands he clutches a blushing pink sundress. It's a simple thing--thin straps, a row of delicate buttons, a hem that ends a couple inches above the knees--but just the vague thought of the dress caressing his skin causes the blood to rise to his cheeks, a deep heat that he's sure would give him away if anyone was watching. Of course, no one is watching, he wouldn't be so careless. Dad's gone, in another state probably, and Dean's out, maybe trying to find a job or picking up a girl or just getting a couple whiskeys at the bar with his fake I.D.. Regardless, Sam had brought his whole bag (with the dress buried at the bottom, under the lining) into the motel bathroom and locked the door behind him. His hands shake subtly, like a blade of grass on a breezy autumn day, as he unfurls the garment, letting it hang in front of his knobby-kneed, slender frame as he peers at himself in the mirror. The color compliments him; his skin, tanned from years outside training with Dad and wrestling with Dean, a perfect match for the gentle hue. He steps into the dress, pulling it up easily past his slim hips, arms threading through the straps like a needle stitching fabric.

The dress is cut for a woman: more room on the chest, cinching on the waist, effortless flare on the hips. With this dress that gives the illusion of curves, with his blood-tinted cheeks and eyelashes thick and dark, he looks girly. His barely-shaggy brown hair even, when paired with all this, looks pixie-ish and feminine. It takes his breath away, looking into that grimy motel mirror, seeing what could have been, what still could be. Sam sways back and forth, regarding himself in every angle, turning around and looking over his shoulder to peer at his backside. Sam's dilated eyes reflect back at him, excitement shining, and a small, secret smile cracks his lips. He spins on his tip-toes, once, twice, the dress fanning out around him like a hula hoop. A startled, ecstatic laugh breaks from his throat as he settles back in front of the mirror, his hands clasped sweetly in front of him. He stands there for a long time, his hazel eyes sometimes roving and sometimes settling on a flattering region.

After a while, hours, years, God knows how long, the motel door unlocks, harsh sound startling Sam out of his reverie. He gasps, quietly, when Dean calls out "Sammy!" He can hear Dean's boot-clad footsteps crossing the room and he's wiggling out of the dress in record time, pulling on hand-me-down jeans and t-shirt in its place. His heart is thumping raggedly in his ears and Dean knocks on the bathroom door, tugs on the locked handle. "Sammy? C'mon, I really need to take a shower." Sam takes just another moment to pack his dress back in the bag and sling it over his shoulder, to center himself before he reaches out and clicks the lock. His big brother stands there, obstructing the doorway, eyes immediately inspecting the younger brother's face for signs of trouble. Sam forces the most calm, neutral expression he can manage before ducking out from under Dean, who smells like sex, alcohol, and a flowery perfume. Girls and whiskey, then, Sam thinks errantly.

"Hey, hold up," Dean says, turning around to watch his brother's retreat. Sam looks back at him, barely meeting his brother's eyes, which flick to the bag hanging on Sam's shoulder, questioning. "You okay?" He asks, heavy gaze landing on the younger Winchester and refusing to let Sam look away. "I'm fine, De, go shower. You stink," Sam answers in his most put-upon voice, compelling annoyance into his tone so he is not betrayed by the fear he feels. Dean considers him for another moment, Sam's anxiety nearly boiling over, before he quirks a smile and dips into the bathroom. Sam exhales in relief when he hears the door close and the shower start, flopping down onto his back on the mattress and trying to slow his racing heart.

He thinks of the dress again on his willowy frame, the way he looked graceful and alluring, and he closes his eyes, smiling at the ceiling. It's not long before he starts to crave the feeling of the pink material on his skin again.

**Author's Note:**

> I've been reading fics for years but this is the first I've ever written. I have to write 365 words a day for my college writing class and I wans't inspired by anything today, so I went to a prompt generator and got "First Time Wearing a Dress". Please leave a comment if you feel like it :)


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